238: This is Part 1 of one of the most philosophical conversations ever recorded on In My Non-Expert Opinion with Chelsea’s vision board guest, Derek Sivers.

In this episode, Chelsea and Derek discuss:

• Derek’s nomadic heart and values, and how his decision to be a good dad led him to halt his travels and settle in New Zealand
• Derek’s goal to make the whole world feel like home
• Inhabiting philosophies from around the world
• Useful, not true, thinking
• Constantly pivoting to find your own success
• How to make decisions that actually align with your goals
• Creating just for the sake of it vs. monetizing
• The power of constraints

• and WAY more eye-popping, quotable gems from Derek

Resources Mentioned:

• "Personal Development for Smart People" by Steve Pavlina
• Derek's books
• Four Thousand Weeks by Oliver Burkeman
• Midnight Library by Matt Haig

Connect with Derek:

• Website

Connect with Chelsea:

• Website
• 1:1 Podcast Coaching

• Instagram
• Slight Turbulence Substack - the travel magazine you wish existed on the back of airplane seats
• Pitch Perfect Bootcamp - Round 2 Waitlist

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Want to send a voice note to the podcast and have Chelsea answer yo

Connect with Chelsea:

• 🪐 Pitch Perfect Fall 2026 Waitlist
• ☄️ SUPERNOVA waitlist: the thinking lab for the deep thinkers, world-builders, and curious visionaries who see futures that don't exist yet. 
• 💻 Website
• 🍿Popcorn Club: Monthly meet-up to debrief TV, movies, and the zeitgeist
• 📜 Footnotes newsletter filled with rabbit holes
• 💌 The Art of the Ask Podcast
• 📱 IG: ⁠@chelseariffe⁠
• 🧵 Threads: @chelseariffe

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